5-Bromovanillin

Base Information

• Chemical Name: 5-Bromovanillin
• CAS No.: 2973-76-4
• Molecular Formula: C8H7BrO3
• Molecular Weight: 231.046
• Hs Code.: 29130000
• European Community (EC) Number: 221-016-6
• NSC Number: 29037,10073
• UNII: 508WVS56PW
• DSSTox Substance ID: DTXSID7022203
• Nikkaji Number: J30.765C
• Wikidata: Q21045306
• Metabolomics Workbench ID: 137049
• ChEMBL ID: CHEMBL467332
• Mol file: 2973-76-4.mol

Synonyms:3-bromo-4-hydroxy-5-methoxy-benzaldehyde;Vanillin, 5-bromo-;Benzaldehyde, 3-bromo-4-hydroxy-5-methoxy-;5-Bromo vanillin;5-Bromovanillin 97%;5-Bromo-4-hydroxy-3-methoxybenzaldehyde;3-bromo-4-hydroxy-5-methoxybenzaldehyde;

Chemical Property of 5-Bromovanillin

Chemical Property:

• Appearance/Colour: light brown crystalline powder
• Vapor Pressure: 1.47E-05mmHg at 25°C
• Melting Point: 164-166 °C(lit.)
• Refractive Index: 1.62
• Boiling Point: 289.5 °C at 760 mmHg
• PKA: 6.26±0.23(Predicted)
• Flash Point: 128.9 °C
• PSA: 46.53000
• Density: 1.653 g/cm³
• LogP: 1.97580
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air & Light Sensitive
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 229.95786
• Heavy Atom Count: 12
• Complexity: 162

Purity/Quality:

99% ^*data from raw suppliers

5-Bromovanillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39-22-24/25-20/21

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C(=CC(=C1)C=O)Br)O
• Uses: 5-Bromovanillin was used to enrich the metabolically stable anaerobic cultures to study dechlorination of chlorocatechols. It was also used to prepare 2, 5-dihydroxy-4-methoxy-6-bromobenzaldehyde and 5-bromovanillate.

Technology Process of 5-Bromovanillin

There total 29 articles about 5-Bromovanillin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

vanillin (121-33-5,8014-42-4) → 3-bromo-4,5-dihydroxybenzaldehyde (16414-34-9) + 2,3-dibromo-4,5-dihydroxybenzylaldehyde (14045-41-1) + 2-Methoxy-4,5,6-tribromophenol (38926-85-1) + 5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4)

Guidance literature:

With sulfuric acid; dihydrogen peroxide; bromine; In dichloromethane; at 45 ℃; for 2h; Further byproducts given;

DOI:10.1007/BF01151189

Reference yield: 94.0%

C8H7BF3O3(1-)*K(1+) → 5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4)

Guidance literature:

With tetra-N-butylammonium tribromide; In tetrahydrofuran; water; at 20 ℃; for 0.666667h; chemoselective reaction;

DOI:10.1016/j.tet.2012.03.016

Reference yield: 86.2%

di-isopropyl ether (108-20-3) + vanillin (121-33-5,8014-42-4) → 5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4)

Guidance literature:

upstream raw materials:

N-Bromosuccinimide

chloroform

vanillin

1-methyl-4-nitrosobenzene

Downstream raw materials:

1-(3-bromo-4-hydroxy-5-methoxy-phenyl)-propan-1-ol

3-bromo-4'-chloro-4-hydroxy-5-methoxy-trans-chalcone

4-(5-bromo-4-hydroxy-3-methoxyphenyl)buten-2-one

3-bromo-4-hydroxy-5-methoxy-α-methylamino-benzyl alcohol

Refernces

• 1、 G?hl, Matthias,Seifert, Karlheinz. "Synthesis of the Sesquiterpenes Albicanol, Drimanol, and Drimanic Acid, and the Marine Sesquiterpene Hydroquinone Deoxyspongiaquinol". . p. 6975 - 6982. Retrieved 2014.
• 2、 Setyawati, Amri,Wahyuningsih, Tutik Dwi,Purwono, Bambang. "Syntheses of novel pyrazolines as antibacterial agents from natural product vanillin". . p. 454 - 456. Retrieved 2017.
• 3、 Damodar, Kongara,Shin, Sooyong,Jeon, Sung Ho,Lee, Jeong Tae. "First synthesis of tabamides A–C and their derivatives: In vitro nitric oxide inhibitory activity". supporting information. . Retrieved 2021/11/10.
• 4、 -. "Bromophenol-pyrazoline compound as well as synthesis method and application thereof (by machine translation)". Paragraph 0026-0029. . Retrieved 2020/11/12.